What Fear of Failure Teaches Us About Leadership
As an executive coach, I speak with many leaders—some of the most capable and committed people you can imagine. They’re leading organizations making an incredible impact on social and environmental issues. They’re driving high-performing teams and monumental change.
Yet, when they come to coaching, they often share what they can’t say anywhere else: their fears.
Beneath the surface of most leadership challenges lies a quiet concern—
“If I do the wrong thing, I’ll fail my team, my mission, and myself.”
The situations vary:
A team that isn’t yet performing at the level needed.
A direct report who needs a difficult conversation.
An outdated system that’s slowing down operations.
Tough feedback from a board or funder.
The constant juggle of raising money, meeting expectations, and delivering outcomes.
Leaders know they must act. They understand that inaction has costs. But seasoned leaders—those who’ve been around long enough to see the fallout from past decisions—often carry a deeper fear:
“If I make the wrong call, I’ll lose respect.”
“If I fail, people will see I’m not capable.”
“If I push for change, there could be backlash.”
How Fear of Failure Shows Up
Fear of failure doesn’t always look like fear. It can look like:
Over-control or micromanagement: Needing to manage every detail so nothing goes wrong.
Perfectionism: Tweaking endlessly, never feeling ready.
People-pleasing: Prioritizing harmony over honesty.
Risk aversion: Choosing safe, familiar paths instead of innovation.
Overworking: Believing effort alone will protect against failure.
Avoidance: Steering clear of stretch opportunities that might expose vulnerability.
When leaders operate from this place, teams feel it. Psychological safety erodes. Innovation stalls. Feedback loops close. The organization becomes cautious—and the leader’s own growth plateaus.
Fear of failure is contagious. It can quietly shape a culture of caution.
A Different Relationship with Failure
When I coach leaders through high-stakes decisions, we often start not with the options on the table, but with a simple reflection:
“What do I fear most about moving forward?”
This question surfaces the real barrier—the story underneath the strategy.
And the follow-up question brings clarity:
“What is the consequence of not taking action?”
I’ve seen this pattern play out many times:
A leader avoids addressing a performance issue, only to watch a program weaken.
Another over-functions to ensure success, unintentionally disempowering their team.
A third delays restructuring for better alignment, fearing disruption more than stagnation.
Reframing Failure
The shift happens when leaders redefine what failure means.
Failure isn’t a verdict—it’s feedback. It’s part of learning, leading, and evolving. Courageous leaders don’t eliminate fear; they move with it. They recognize that progress often looks messy, that growth often feels uncertain, and that real leadership means taking action even when outcomes aren’t guaranteed.
When leaders model this mindset, they give their teams permission to do the same—to experiment, learn, and stretch. Because the real failure isn’t in falling short. It’s in standing still.